I may be early, but here's a list of my favorite winter songs. (Most of which are related to Christmas.)
Unlike my Autumn list, there are bound to be some songs on here that are repeats from last year, but that just means they're so good that they withstand the test of time!
Walking in the air [link] (this particular cover is done by Chloe Agnew) for something eerie and magical.
Two of Ruth Moody's songs:
1. Cold Outside [link] For something calm
2. Winter Waltz [link] Ditto.
Three of Straight No Chaser's songs:
1. Christmas Can-Can [link] for ample amounts of hilarity!
2. Who Spiked the Eggnog [link] for a fun 'whodunit' song
3. Hey Santa [link] for something jazzy and sexy.
Four of the Barenaked Ladies' songs:
1. Jingle Bells [link] for a fun take on a classic Xmas carol.
2. Footprints [link] for something calm but hopeful
3. The Snowman's song [link] for a sad winter song (sorry, this was the only version I could find)
4. Elf's Lament [link] for something funny with a bit of snark
The Barenaked Ladies also have a couple Hanukkah songs, for those of you who celebrate it.
Three songs by Sarah McLachlan:
1. River [link] for something sad
2. Wintersong [link] for something dreamy
3. Song for a Winter's Night [link] ditto.
Celtic Carol by one of my favorite ladies, Lindsey Stirling [link] for something fun and spirited.
Two Amy Grant songs:
A Christmas to Remember [link] for something festive.
Breath of Heaven [link] for something tear-jerking.
...Actually, there's a whole playlist included in the second link, so check out her stuff at your leisure!
The Christmas Shoes (not sure who the singer is) [link] for something that will probably make you cry.
The Piano Guys Christmas playlist:
[link] These guys are just generally awesome!
February Song [link] by Josh Groban, depending on whether or not you think February is a part of winter.
This is already a long list, but I'll add more when I think of them.